Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester
• CAS No.: 708253-89-8
• Molecular Formula: C₁₉H₃₃NO₄SSi
• Molecular Weight: 399.627
• Mol file: 708253-89-8.mol

Synonyms:Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester

Chemical Property of Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester

There total 3 articles about Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2S,4R)-1-benzyl-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid methyl ester (154429-40-0) → Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester (708253-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiBH₄ / tetrahydrofuran

2.1: trifluoroacetic anhydride

2.2: diisopropylethylamine

3.1: pyridine

With pyridine; lithium borohydride; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2004.02.034

Reference yield:

(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin (154343-02-9) → Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester (708253-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic anhydride

1.2: diisopropylethylamine

2.1: pyridine

With pyridine; trifluoroacetic anhydride;

DOI:10.1016/j.bmcl.2004.02.034

Reference yield:

methanesulfonyl chloride (124-63-0) + (3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol (161564-09-6) → Methanesulfonic acid (3R,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxy)-piperidin-3-yl ester (708253-89-8)

Guidance literature:

DOI:10.1081/NCN-120022747

upstream raw materials:

methanesulfonyl chloride

(3R,5R)-1-benzyl-5-[(tert-butyldimethylsilyl)oxy]-piperidin-3-ol

(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin

(2S,4R)-1-benzyl-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

[3-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-tert-butoxycarbonylamino-piperidin-1-yl]-acetic acid ethyl ester

tert-butyl N-[(3S,5R)-1-benzyl-5-[tert-butyl(dimethyl)silyl]oxy-3-piperidyl]carbamate

[(3R,5S)-5-azido-1-benzyl-3-piperidyl]oxy-tert-butyl-dimethylsilane